Azo disperse dyes having 1,2,4-triazol-5-yl diazo component radicals having electron-withdrawing substituents in the 3-positions

ABSTRACT

Compounds of the formula ##STR1## wherein R 1  is C 1-18  alkyl, substituted C 1-18  alkyl, phenyl, substituted phenyl, C 3-6  alkenyl, substituted C 3-6  alkenyl, C 3-6  alkynyl or substituted C 3-6  alkynyl, 
     R 2  is an electron withdrawing substituent; and 
     K is the residue of a coupling component that is free of any water solubilizing groups. 
     The compounds are disperse dyes which can be used to dye, print or pad fully synthetic or semi-synthetic hydrophobic high molecular weight organic material.

According to the invention there is provided a compounds of formula I ##STR2## in which R₁ is selected from C₁₋₁₈ alkyl, phenyl, C₂₋₆ alkenyl and C₂₋₆ alkynyl, each being unsubstituted or substituted;

R₂ is an electron-withdrawing substituent; and

K is the residue of a coupling component that is free of water-solubilizing groups.

The compounds of formula I are good disperse dyes and can be used to dye, print or pad fibers or threads or material formed from fibers or threads of fully synthetic or semisynthetic hydrophobic high molecular weight organic material.

Water-solubilizing groups include --SO₃ H and COOH.

The compounds of formula I are useful for transfer printing as described in U.S. Pat. Nos. 4,720,480 and 4,820,686 and EP 194,106.

R₁ is preferably R₁ ' where R₁ ' is

C₁₋₄ alkyl, unsubstituted or substituted by one to three (preferably one) groups selected from cyano, hydroxy, C₁₋₄ alkoxycarbonyl, C₁₋₄ alkylcarbonyl, C₁₋₄ alkylcarbonyloxy, C₁₋₄ alkoxycarbonyloxy, aminocarbonyl, C₁₋₄ alkoxy, halogen, formyl and formyloxy;

C₂₋₆ alkynyl or C₂₋₆ alkenyl optionally substituted by halogen or a phenyl group; or phenyl, unsubstituted or substituted by one or two groups selected from halogen, C₁₋₄ alkoxy, nitro or C₁₋₄ alkoxycarbonyl; benzyl unsubstituted and substituted by 1 or 2 halogen.

More preferably R₁ is R₁ " where R₁ " is C₁₋₄ alkyl, cyano-(C₁₋₄ alkyl), C₁₋₂ alkoxycarbonylmethyl, allyl, chloroallyl, dinitrophenyl, benzyl or dichlorobenzyl. Most preferably R₁ is R₁ " where R₁ " is dichlorobenzyl.

Preferably R₂ is R₂ ' where R₂ ' is trifluoromethyl, halogen, monochloromethyl, monobromomethyl, dichloromethyl, dibromomethyl, trichloromethyl, tribromomethyl, formyl, aminocarbonyl, cyano, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, carboxyl, C₂₋₆ alkenyl bearing a phenyl, a C₁₋₆ alkoxycarbonyl or a carboxyl group or C₂₋₆ alkynyl bearing a phenyl, a C₁₋₆ alkoxycarbonyl or a carboxyl group. More preferably R₂ is R₂ " where R₂ " is trifluoromethyl.

K is preferably K' where K' is a coupling component of the aniline, naphthylamine, naphthol, pyridine, pyridone, pyrazole, pyrazolone, pyrimidone, tetrahydroquinoline, benzomorpholine, pyrrole, coumarin, thiazole, indole, carbazole or oxazole series or the residue of a coupling component having an active methylene group.

More preferably K is K" where K" is a group of formula V ##STR3## in which R₃ is hydrogen, C₁₋₄ alkyl (preferably methyl or ethyl), C₁₋₄ alkoxy (preferably methoxy or ethoxy) or halogen;

R₄ is hydrogen, C₁₋₄ alkyl, C₁₋₄ acyl (preferably --CO--C₁₋₄ alkyl), benzoylamino, C₁₋₄ alkylcarbonylamino, C₁₋₄ alkoxycarbonylamino, C₁₋₄ alkylsulphonylamino, acryloylamino, or C₃₋₄ alkenylcarbonylamino, in which any alkyl group present in R₄ can be unsubstituted or substituted by one group selected from halogen, hydroxy, C₁₋₄ alkoxy, phenyl and phenoxy;

R₅ is C₁₋₈ alkyl, unsubstituted or substituted by one or two conventional substituent groups (such as cyano, halogen, hydroxy, C₁₋₄ alkoxy, phenyl, C₁₋₄ alkylcarbonyloxy, C₁₋₄ alkoxycarbonyl, phenoxycarbonyl and phenoxy), C₃₋₈ alkenyl, unsubstituted or substituted by halogen or phenyl, C₃₋₈ alkynyl, unsubstituted or substituted by halogen or phenyl; cyclohexyl, unsubstituted or substituted by one to three C₁₋₄ alkyl (preferably methyl) groups; or phenyl, unsubstituted or substituted by halogen, C₁₋₄ alkyl (preferably methyl) or C₁₋₄ alkoxy (preferably methoxy or ethoxy);

R₆ is hydrogen, C₁₋₈ alkyl, unsubstituted or unsubstituted by one or two conventional substituent groups (preferably such conventional substituent groups are selected from halogen, cyano, hydroxy, C₁₋₄ alkoxycarbonyl, C₁₋₄ alkylcarbonyl, C₁₋₄ alkylcarbonyloxy, C₁₋₄ alkoxycarbonyloxy, aminocarbonyl, C₁₋₄ alkoxy, halogen, formyl and formyloxy, C₃₋₈ alkenyl, unsubstituted or substituted by halogen; or C₃₋₈ alkynyl, unsubstituted or substituted by halogen; or

R₅ and R₆ together with the N atom to which they are attached form a heterocyclic group.

Preferably R₃ is R₃ ' where R₃ ' is hydrogen, methyl or ethyl, more preferably hydrogen.

Preferably R₄ is R₄ ' where R₄ ' is hydrogen, methyl, C₁₋₂ alkylcarbonylamino, acryloylamino, benzoylamino or C₁₋₂ alkylsulphonylamino.

Preferably R₅ is R₅ ' where R₅ ' is selected from allyl, chloroallyl, C₁₋₄ alkyl and C₂₋₄ alkyl, substituted by one substituent selected from methoxy, ethoxy, C₁₋₂ alkylcarbonyloxy, C₁₋₂ alkoxycarbonyl, cyano and phenoxycarbonyl.

More preferably R₅ is R₅ " where R₅ " is selected from ethyl, cyanoethyl, acetoxyethyl, allyl and chloroallyl.

Preferably R₆ is R₆ ' where R₆ ' is selected from allyl, chloroallyl, C₁₋₄ alkyl and C₂₋₄ alkyl, substituted by one substituent selected from methoxy, ethoxy, C₁₋₂ alkylcarbonyloxy, C₁₋₂ alkoxycarbonyl and cyano.

More preferably R₆ is R₆ " where R₆ " is ethyl, cyanoethyl, acetoxyethyl or chloroallyl.

Compounds of formula I can be prepared by alkylating or arylating an azo compound of formula II ##STR4## with an R₁ -containing compound or with an alkylating or arylating agent which introduces an R₁ group.

Alkylation and arylation can be carried out by known methods. Known alkylating and arylating agents include C₁₋₁₈ alkyl halides, C₁₋₁₈ alkylsulphates, epoxides, α- and β-unsaturated compounds or (Di) nitrochlorobenzene.

The compounds of formula II can be made by diazotising one mole of an amine of formula III ##STR5## and coupling with one mole of a coupling component of formula IV

    H-K                                                        (IV)

where the symbols are as defined above.

Compounds of formula I can be worked into dyeing preparations by known methods, for example by milling in the presence of a dispersing or filling agent. The preparations can be dried under vacuum or pulverized and can be used with much or little water to dye in short or long baths by exhaust dyeing padding or printing.

The dyes of formula I exhaust very well from aqueous suspensions and are suitable for coloring synthetic or semisynthetic, hydrophobic, high molecular weight textile material. Such textile material especially includes linear, aromatic polyester as well as cellulose 21/2 acetate, cellulose triacetate and synthetic polyamide.

Dyeing can be carried out by known methods, for example in the process of GB Patent 1,114,433, the contents of which are incorporated herein by reference.

The resulting dyeings show good fastness properties, especially good light fastness properties, good thermofixation properties, good sublimation fastness properties and good blistering properties.

The dyes of the invention have good thermal transfer printing, good migration, good dyeing depth, good stability and good light fastness properties.

In this specification halogen is preferably fluoro, chloro, bromo or iodo, preferably chloro or bromo. Preferably any C₁₋₆ alkyl or C₁₋₆ alkyl groups are C₁₋₄ alkyl or C₁₋₄ alkoxy groups, respectively, more preferably methyl or ethyl or methoxy and ethoxy, respectively.

The invention will now be illustrated by the following example in which all parts and percentages are by weight and all temperatures are in °C. unless indicated to the contrary.

EXAMPLE 1

15.5 parts of trifluoromethyl-5-amino-1,2,4-triazole are dissolved in 45 parts of ortho phosphoric acid, are diazotised at -5° with 35 parts of a 40% nitrosylsulphuric acid solution and are then stirred for 2 hours. Whilst maintaining the resulting diazonium solution at 0°, it is added slowly to a solution of 3-acetylamino-N,N-diethylaminobenzene in 200 parts of dilute hydrochloric acid (also kept cool at 0°). The resulting azo compound precipitates out by the addition of 30% sodium hydroxide and ice, after which the mixture is filtered and washed to be acid free.

23 parts of the resulting dried compound are suspended in 100 parts of acteone, reacted with 5 parts of potassium carbonate and 6.5 parts of benzyl chloride and boiled for 3 hours under reflux. After cooling to room temperature, the resultant dyestuff precipitates out, is filtered washed salt free and dried.

The compound of formula 1a results ##STR6##

EXAMPLES 2-64

Compounds of the formula ##STR7## in which R₁ to R₆ are defined in Table 1 below can be made by a method analogous to that of Example 1 from known compounds. The compounds of Examples 1 to 64 dye polyester a yellow to reddish-yellow tone.

Any C₂ H₄ group in the Examples is --CH₂ CH₂ --.

Any --OCO-- radical is a --O--CO-- radical.

The compounds of Examples 1 to 88 are single compounds not mixtures, but the position of R₁ was not clarified.

                                      TABLE I                                      __________________________________________________________________________     Ex.                                                                            No.                                                                               R.sub.1  R.sub.2    R.sub.3                                                                             R.sub.4   R.sub.5    R.sub.6  λ.sub.max                                                               . nm                 __________________________________________________________________________      1 --CH.sub.2 C.sub.6 H.sub.5                                                              --CF.sub.3 H    --NHCOCH.sub.3                                                                           --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       498                   2 "        "          --OC.sub.2 H.sub.5                                                                  "         --CH.sub.2 CH═CH.sub.2                                                                --CH.sub.2 CH═CH.sub.                                                      2        527                   3                                                                             n-C.sub.4 H.sub.9                                                                 "        "          "    "         "          518                            4 --CH.sub.2 CH═CHCl                                                                  "          "    "         "          "        525                   5 --CH.sub.2 CN                                                                           "          H    "         --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       504                   6 --CH.sub.2 CO.sub.2 CH.sub.3                                                            "          H    "         --C.sub.2 H.sub.4 OCH.sub.3                                                               --C.sub.2 H.sub.4                                                              OCH.sub.3                                                                               500                   7 2,4-Dichloro-                                                                           "          H    "         "          "        498                     benzyl                                                                        8                                                                               "        "          H    "         --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       502                   9 "        --Cl       H    "         "          "        499                  10 --CH.sub.2 C.sub.6 H.sub.5                                                              --CHCl.sub.2                                                                              H    "         "          "        490                  11 "        --CH.sub.2 Cl                                                                             H    "         --C.sub.3 H.sub.7 (n)                                                                     --C.sub.3 H.sub.7                                                                       485                  12 "        --CHO      H    "         --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       500                  13 "        "          H    --CH.sub.3                                                                               "          "        491                  14 "        --CN       H    --NHCOCH.sub.3                                                                           "          "        512                  15 "        "          H    "         --C.sub.2 H.sub.4 OCOCH.sub.3                                                             --C.sub.2 H.sub.4                                                              OCOCH.sub.3                                                                             505                  16 "        --CHO      H    "         --CH.sub.2 CH═CH.sub.2                                                                --C.sub.2 H.sub.4                                                              OCH.sub.3                                                                               496                  17 "        "          H    "         "          --C.sub.2 H.sub.4                                                                       488                  18 "        "          H    --NHCOC.sub.6 H.sub.5                                                                    --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       502                  19 "        "          H    --NHCOCH═CH.sub.2                                                                    "          "        505                  20 "        --CN       H    --NHSO.sub.2 CH.sub.3                                                                    "          "        510                  21 "        --CONH.sub.2                                                                              H    --NHCOC.sub.2 H.sub.5                                                                    --CH.sub.2 CH═CHCl                                                                    --C.sub.2 H.sub.4                                                              OCH.sub.3                                                                               493                  22 "        --COOH     H    --NHCOCH.sub.3                                                                           --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       498                  23 "        --CH═CH--COOH                                                                         H    "         "          "        --                   24 "        --CH═CH--C.sub.6 H.sub.5                                                              H    "         "          "        --                   25 2,4-Dinitro-                                                                            --CF.sub.3 H    --NHCOCH.sub.3                                                                           --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       510                     phenyl                                                                      26 --CH.sub.2 CH.sub.2 --CN                                                                "          H    "         "          "        503                  27 --CH.sub.2 C.sub.6 H.sub.5                                                              "          H    --CH.sub.3                                                                               "          "        490                  28 "        "          H    H         "          "        485                  29 "        "          H    --NHCOCH.sub.3                                                                           --C.sub.2 H.sub.4 OCOCH.sub.3                                                             --C.sub.2 H.sub.4                                                                       484                  30 "        "          H    "         "          --C.sub.2 H.sub.4                                                              OCOCH.sub.3                                                                             490                  31 "        "          H    H         --C.sub.2 H.sub.4 CN                                                                      "        467                  32 "        "          H    --CH.sub.3                                                                               "          "        476                  33 "        "          H    H         --C.sub.2 H.sub.4 OCOCH.sub.3                                                             "        478                  34 "        "          H    H         --C.sub.2 H.sub.4 CO.sub.2 C.sub.2                                             H.sub.5    --C.sub.2 H.sub.4                                                              CO.sub.2 C.sub.2                                                                        477ub.5              35 2,4-Dichloro-                                                                           "          H    --CH.sub.3                                                                               --C.sub.2 H.sub.5                                                                         --C.sub.2 H.sub.5                                                                       494                     benzyl                                                                      36 "        "          H    H         "          "        488                  37 "        "          H    --NHCOCH.sub.3                                                                           --C.sub.2 H.sub.4 OCOCH.sub.3                                                             --C.sub.2 H.sub.4                                                                       486                  38 "        "          H    "         "          --C.sub.2 H.sub.4                                                              OCOCH.sub.3                                                                             494                  39 "        "          H    H         --C.sub.2 H.sub.4 CN                                                                      "        469                  40 "        "          H    --CH.sub.3                                                                               "          "        478                  41 "        "          H    H         --C.sub.2 H.sub.4 OCOCH.sub.3                                                             "        482                  42 "        "          H    H         --C.sub.2 H.sub.4 CO.sub.2 C.sub.2                                             H.sub.5    --C.sub.2 H.sub.4                                                              CO.sub.2 C.sub.2                                                                        481ub.5              43 --CH.sub.2 CH═CHCl                                                                  "          H    --CH.sub.3                                                                               --C.sub.2 H.sub.4 OCOCH.sub.3                                                             --C.sub.2 H.sub.4                                                                       474                  44 "        "          H    H         "          "        466                  45 "        "          H    --NHCOCH.sub.3                                                                           "          "        483                  46 "        "          H    H         --C.sub.2 H.sub.4 CO.sub.2 C.sub.2                                             H.sub.5    --C.sub.2 H.sub.4                                                              CO.sub.2 C.sub.2                                                                        478ub.5              47 2,4-Dichloro-                                                                           "          H    --NHCOCH.sub.3                                                                           --CH.sub.2 CH═CH.sub.2                                                                --C.sub.2 H.sub.4                                                              OCH.sub.3                                                                               494                     benzyl                                                                      48 --CH.sub.2 CH.sub.2 CN                                                                  --CF.sub.3 H    --CH.sub.3                                                                               --C.sub.2 H.sub.4 OCOCH.sub.3                                                             --C.sub.2 H.sub.4                                                                       477                  49 "        "          H    H         "          "        468                  50 "        "          H    --NHCOCH.sub.3                                                                           "          "        486                  51 "        "          H    H         --C.sub.2 H.sub.4 CO.sub.2 C.sub.2                                             H.sub.5    "        485                  52 "        "          H    --NHCOCH.sub.3                                                                           --CH.sub.2 CH═CH.sub.2                                                                --C.sub.2 H.sub.4                                                              OCH.sub.3                                                                               496                  53 --CH.sub.2 C.sub.6 H.sub.5                                                              "          H    --CH.sub.3                                                                               --CH.sub.2 --CH═CHCl                                                                  --C.sub.2 H.sub.4                                                                       476                  54 "        "          H    H         "          "        467                  55 "        "          H    NHCOCH.sub.3                                                                             "          "        484                  56 2,4-Dichloro-                                                                           "          H    "         "          "        487                     benzyl                                                                      57 "        "          H    --CH.sub.3                                                                               "          "        478                  58 "        "          H    H         --C.sub.2 H.sub.5                                                                         "        479                  59 "        "          H    --CH.sub.3                                                                               --CH.sub.2 --CH═CHCl                                                                  --CH.sub.2 CH═CHCl                                                                  482                  60 "        "          H    --NHCOCH.sub.3                                                                           "          "        490                  61 "        "          H    H         "          "        474                  62 --CH.sub.2 C.sub.6 H.sub.5                                                              "          H    --NHCOCH.sub.3                                                                           "          "        488                  63 2,4-Dichloro-                                                                           "          H    "         "          --C.sub.2 H.sub.5                                                                       495                     benzyl                                                                      64 "        "          H    "         "          --C.sub.2 H.sub.4                                                              OCOCH.sub.3                                                                             491                  __________________________________________________________________________

EXAMPLES 64-88

Compounds of the formula ##STR8## in which R₁ and K are defined in Table 2 below can be prepared by a method analogous to that of Example 1 from known compounds. The dyeings using the compounds of Examples 64-88 colour polyester a yellow to light reddish-yellow tone.

                  TABLE II                                                         ______________________________________                                         Ex.                   K (coupling component                                    No.  R.sub.1          radical)        λ .sub.max.                       ______________________________________                                         65   CH.sub.2 C.sub.6 H.sub.5                                                                         ##STR9##       413                                      66                                                                                   ##STR10##       "               415                                      67   "                                                                                                ##STR11##      440                                      68   "                                                                                                ##STR12##      445                                      69   CH.sub.2 C.sub.6 H.sub.5                                                                         ##STR13##      436                                      70   CH.sub.2 C.sub.6 H.sub.5                                                                         ##STR14##      491                                      71   "                                                                                                ##STR15##      431                                      72   2,4-Dichlorobenzyl                                                                              "               434                                      73   CH.sub.2 CHCHCl                                                                                  ##STR16##      434                                      74   "                                                                                                ##STR17##      428                                      75   "                                                                                                ##STR18##      411                                      76   CH.sub.2 CH.sub.2 CN                                                                             ##STR19##      412                                      77   CH.sub.2 CN                                                                                      ##STR20##      442                                      78   CH.sub.2 CH.sub.2 CN                                                                            "               439                                      79   2,4-Dichlorobenzyl                                                                               ##STR21##      418                                      80   "                                                                                                ##STR22##      410                                      81   2,4-Dichlorobenzyl                                                                               ##STR23##      410                                      82   CH.sub.2 C.sub.6 H.sub.5                                                                         ##STR24##      406                                      83   "                                                                                                ##STR25##      430                                      84   2,4-Dichlorobenzyl                                                                               ##STR26##      438                                      85   2,4-Dichlorobenzyl                                                                               ##STR27##      425                                      86   "                                                                                                ##STR28##      405                                      87   CH.sub.2 C.sub.6 H.sub.5                                                                        "               403                                      88   "                                                                                                ##STR29##      435                                      ______________________________________                                    

Application Example

7 parts of the dyestuff of Example 1 (Compound 1a) is milled with 13 parts of sodium ligninsulphonate, 25 parts of water and 100 parts of silica quartz beads until the particle size of the dyestuff is on average less than 1 μm. The silica beads are then filtered off from the suspension and the remaining suspension is dried under mild conditions and then pulverised. 1 part of the resulting preparation is stirred into 4000 parts of warm (60°) water buffered at pH 5. With this dyebath, 100 parts of polyester fibre material is dyed with the addition of 20 parts of o-phenylphenol for 1 hour at 98°. After cooling, washing, soaping, and washing and drying a second time, a level reddish-yellow dyeing results with good dyeing properties.

The Application Example can be repeated using, instead of compound 1a, 7 parts of any one of the dyes of Examples 2 to 88. 

I claim:
 1. A compound of the formula ##STR30## wherein K is a coupling component radical free of water-solubilizing groups,R₁ is C₁₋₁₈ alkyl, substituted C₁₋₁₈ alkyl, phenyl, substituted phenyl, C₂₋₆ alkenyl, substituted C₃₋₆ alkenyl, C₂₋₆ alkynyl or substituted C₃₋₆ alkynyl, and R₂ ' is halo; chloromethyl; bromomethyl; dichloromethyl; dibromomethyl; trifluoromethyl; trichloromethyl; tribromomethyl; cyano; aminocarbonyl; formyl; (C₁₋₆ alkyl)carbonyl; (C₁₋₆ alkoxy)carbonyl; C₂₋₆ alkenyl monosubstituted by phenyl, (C₁₋₆ alkoxy)carbonyl or carboxy; or C₂₋₆ alkynyl monosubstituted by phenyl, (C₁₋₆ alkoxy)carbonyl or carboxy.
 2. A compound according to claim 1wherein R₁ is C₁₋₄ alkyl; C₁₋₄ alkyl substituted by one to three substituents selected from cyano, hydroxy, (C₁₋₄ alkoxy)carbonyl, (C₁₋₄ alkyl)carbonyl, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₄ alkoxy)carbonyloxy, aminocarbonyl, C₁₋₄ alkoxy, halo, formyl and formyloxy; C₂₋₆ alkenyl; C₂₋₆ alkenyl monosubstituted by halo or phenyl; C₂₋₆ alkynyl; C₂₋₆ alkynyl monosubstituted by halo or phenyl; phenyl; phenyl substituted by one or two substituents selected from halo, C₁₋₄ alkoxy, nitro and (C₁₋₄ alkoxy)carbonyl; benzyl or benzyl monosubstituted or disubstituted by halo.
 3. A compound according to claim 2wherein R₂ ' is trifluoromethyl.
 4. A compound according to claim 2wherein R₁ is C₁₋₄ alkyl, cyano(C₁₋₄ alkyl), (C₁₋₂ alkoxy)carbonylmethyl, allyl, chloroallyl, dinitrophenyl, benzyl or dichlorobenzyl.
 5. A compound according to claim 4wherein R₂ ' is trifluoromethyl.
 6. A compound according to claim 2wherein K is a coupling component radical of the aniline, naphthylamine, naphthol, pyridine, pyridone, pyrazole, pyrazolone, pyrimidone, tetrahydroquinoline, benzomorpholine, pyrrole, coumarin, thiazole, indole, carbazole or oxazole series or the residue of a coupling component having an active methylene radical.
 7. A compound according to claim 6wherein K is ##STR31## wherein R₃ is hydrogen, C₁₋₄ alkyl, C₁₋₄ alkoxy or halo,R₄ is hydrogen; C₁₋₄ alkyl; C₁₋₄ alkyl monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; C₁₋₄ acyl; C₁₋₄ acyl an alkyl moiety of which is monosubstituted by C₁₋₄ alkoxy, phenyl or phenoxy; benzoylamino; (C₁₋₄ alkyl)carbonylamino; (C₁₋₄ alkyl)carbonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; (C₁₋₄ alkoxy)carbonylamino; (C₁₋₄ alkoxy)carbonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; C₁₋₄ alkylsulfonylamino; C₁₋₄ alkylsulfonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; acryloylamino; (C₃₋₄ alkenyl)carbonylamino or (C₃₋₄ alkenyl)carbonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy, R₅ is C₁₋₈ alkyl; C₁₋₈ alkyl substituted by one or two substituents; C₃₋₈ alkenyl; C₃₋₈ alkenyl substituted by halo or phenyl; C₃₋₈ alkynyl; C₃₋₈ alkynyl substituted by halo or phenyl; cyclohexyl; cyclohexyl substituted by one to three C₁₋₄ alkyl groups; phenyl or phenyl substituted by halo, C₁₋₄ alkyl or C₁₋₄ alkoxy, and R₆ is hydrogen; C₁₋₈ alkyl; C₁₋₈ alkyl substituted by one or two substituents; C₃₋₈ alkenyl; C₃₋₈ alkenyl substituted by halo; C₃₋₈ alkynyl or C₃₋₈ alkynyl substituted by halo or --NR₅ R₆ is a heterocyclic group.
 8. A compound according to claim 7wherein R₄ is hydrogen; C₁₋₄ alkyl; C₁₋₄ alkyl monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; (C₁₋₄ alkyl)carbonyl; (C₁₋₄ alkyl)carbonyl the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; benzoylamino; (C₁₋₄ alkyl)carbonylamino; (C₁₋₄ alkyl)carbonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; (C₁₋₄ alkoxy)carbonylamino; (C₁₋₄ alkoxy)carbonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; C₁₋₄ alkylsulfonylamino; C₁₋₄ alkylsulfonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy; acryloylamino; (C₃₋₄ alkenyl)carbonylamino or (C₃₋₄ alkenyl)carbonylamino the alkyl moiety of which is monosubstituted by halo, hydroxy, C₁₋₄ alkoxy, phenyl or phenoxy, R₅ is C₁₋₈ alkyl; C₁₋₈ alkyl substituted by one or two substituents selected from cyano, halo, hydroxy, C₁₋₄ alkoxy, phenyl, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₄ alkoxy)carbonyl, phenoxycarbonyl and phenoxy; C₃₋₈ alkenyl; C₃₋₈ alkenyl substituted by halo or phenyl; C₃₋₈ alkynyl; C₃₋₈ alkynyl substituted by halo or phenyl; cyclohexyl; cyclohexyl substituted by one to three C₁₋₄ alkyl groups; phenyl or phenyl substituted by halo, C₁₋₄ alkyl or C₁₋₄ alkoxy, and R₆ is hydrogen; C₁₋₈ alkyl; C₁₋₈ alkyl substituted by one or two substituents selected from halo, cyano, hydroxy, (C₁₋₄ alkoxy)carbonyl, (C₁₋₄ alkyl)carbonyl, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₄ alkoxy)carbonyloxy, aminocarbonyl, C₁₋₄ alkoxy, halo, formyl and formyloxy; C₃₋₈ alkenyl; C₃₋₈ alkenyl substituted by halo; C₃₋₈ alkynyl or C₃₋₈ alkynyl substituted by halo.
 9. A compound according to claim 8 wherein R₂ ' is trifluoromethyl.
 10. A compound according to claim 8wherein R₁ is C₁₋₄ alkyl, cyano(C₁₋₄ alkyl), (C₁₋₂ alkoxy)carbonylmethyl, allyl, chloroallyl, dinitrophenyl, benzyl or dichlorobenzyl.
 11. A compound according to claim 10 wherein R₂ ' is trifluoromethyl.
 12. A compound according to claim 8wherein R₃ is hydrogen, methyl, ethyl, methoxy, ethoxy or halo, and R₅ is C₁₋₈ alkyl; C₁₋₈ alkyl substituted by one or two substituents selected from cyano, halo, hydroxy, C₁₋₄ alkoxy, phenyl, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₄ alkoxy)carbonyl, phenoxycarbonyl and phenoxy; C₃₋₈ alkenyl; C₃₋₈ alkenyl substituted by halo or phenyl; C₃₋₈ alkynyl; C₃₋₈ alkynyl substituted by halo or phenyl; cyclohexyl; cyclohexyl substituted by one to three methyl groups; phenyl or phenyl substituted by halo, methyl, methoxy or ethoxy.
 13. A compound according to claim 12wherein R₃ is hydrogen, methyl or ethyl, R₄ is hydrogen, methyl, (C₁₋₂ alkyl)carbonylamino, acryloylamino, benzoylamino or C₁₋₂ alkylsulfonylamino, R₅ is allyl, chloroallyl, C₁₋₄ alkyl or C₂₋₄ alkyl monosubstituted by methoxy, ethoxy, (C₁₋₂ alkyl)carbonyloxy, (C₁₋₂ alkoxy)carbonyl, cyano or phenoxycarbonyl, and R₆ is allyl, chloroallyl, C₁₋₄ alkyl or C₂₋₄ alkyl monosubstituted by methoxy, ethoxy, (C₁₋₂ alkyl)carbonyloxy, (C₁₋₂ alkoxy)carbonyl or cyano.
 14. A compound according to claim 13wherein R₅ is ethyl, cyanoethyl, acetoxyethyl, allyl or chloroallyl, and R₆ is ethyl, cyanoethyl, acetoxyethyl or chloroallyl.
 15. A compound according to claim 14wherein R₅ is ethyl, 2-cyanoethyl, 2-acetoxyethyl, allyl or 3-chloroallyl, and R₆ is ethyl, 2-cyanoethyl, 2-acetoxyethyl or 3-chloroallyl.
 16. A compound according to claim 15wherein R₁ is C₁₋₄ alkyl, cyano(C₁₋₄ alkyl), (C₁₋₂ alkoxy)carbonylmethyl, allyl, chloroallyl, dinitrophenyl, benzyl or dichlorobenzyl.
 17. A compound according to claim 16wherein R'₂ is trifluoromethyl.
 18. A compound according to claim 17 having the formula ##STR32##
 19. A process for dyeing a fully synthetic or semi-synthetic high molecular weight organic substrate comprising applying a compound according to claim 1 to a fully synthetic or semi-synthetic high molecular weight organic substrate, said substrate being fibers or threads or a material formed therefrom.
 20. A fully synthetic or semi-synthetic high molecular weight organic substrate to which a compound according to claim 1 has been applied, said substrate being fibers or threads or a material formed therefrom. 